BE 14106

BE 14106

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BE 14106
Category Antibiotics
Catalog number BBF-03702
CAS 140212-86-8
Molecular Weight 423.59
Molecular Formula C27H37NO3

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Description

BE 14106 is produced by the strain of Streptomyces sp. It has weak anti-Pseudomonas aeruginosa activity and inhibition of mixed lymphocyte reaction (MLR) activity.

Specification

Synonyms BE-14106; GT-32A; 9,10-Dihydroxy-7,15-dimethyl-20-(2-hexenyl)azacycloeicosa-3,5,7,11,13,15,17-heptaen-2-one
IUPAC Name (3Z,5Z,7Z,11Z,13Z,15Z,17Z)-20-[(E)-hex-2-enyl]-9,10-dihydroxy-7,15-dimethyl-1-azacycloicosa-3,5,7,11,13,15,17-heptaen-2-one
Canonical SMILES CCCC=CCC1CC=CC=C(C=CC=CC(C(C=C(C=CC=CC(=O)N1)C)O)O)C
InChI InChI=1S/C27H37NO3/c1-4-5-6-7-17-24-18-11-8-14-22(2)15-9-12-19-25(29)26(30)21-23(3)16-10-13-20-27(31)28-24/h6-16,19-21,24-26,29-30H,4-5,17-18H2,1-3H3,(H,28,31)/b7-6+,11-8-,15-9-,16-10-,19-12-,20-13-,22-14-,23-21-
InChI Key ALYLZDHKQZUVDF-SFDMNNJASA-N

Properties

Appearance Colorless Powder
Antibiotic Activity Spectrum Gram-negative bacteria
Boiling Point 640.5°C at 760 mmHg
Density 0.99 g/cm3

Reference Reading

1. Heronamides G-L, polyene macrolactams from Streptomyces niveus
Nan Ding, Li Han, Yi Jiang, Guiding Li, Zehui Zheng, Bixuan Cao, Peipei Guan, Yu Mu, Bin Lin, Xueshi Huang RSC Adv. 2018 May 9;8(31):17121-17131. doi: 10.1039/c8ra02167h.
Six new polyene macrolactams, heronamides G-L (1-6), one new polyenoic acid derivative, niveamide B (10), together with four known compounds, BE-14106-6 (7), BE-14106 (8), GT32-B (9), and niveamide (11), were isolated from the fermentation broth of Streptomyces niveus. Their planar structures were elucidated by detailed analysis of spectroscopic data. The absolute configurations of compounds 1-6 were determined by calculated ECD spectra and analysis of the possible biosynthetic pathways. Compounds 1-6 and 8-11 did not exhibit any significant antimicrobial activities, cytotoxicities, or inhibitory effects on lipopolysaccharide-induced NO production in BV2 microglial cells.
2. Stereochemical Assignment and Biological Evaluation of BE-14106 Unveils the Importance of One Acetate Unit for the Antifungal Activity of Polyene Macrolactams
Kohei Fujita, Ryosuke Sugiyama, Shinichi Nishimura, Naoki Ishikawa, Midori A Arai, Masami Ishibashi, Hideaki Kakeya J Nat Prod. 2016 Jul 22;79(7):1877-80. doi: 10.1021/acs.jnatprod.6b00250. Epub 2016 Jun 22.
Heronamides are a class of potent antifungal metabolites produced by marine-derived actinomycetes. The number of hydroxy groups and the stereochemistry of the two hydroxylated methine carbons are important for the activity of heronamide C, whereas the effect of the hydrocarbon chains is not known. In this study, the stereochemistry and the biological activity of BE-14106, another member of the heronamide class of antibiotics, isolated from an actinomycete Actinoalloteichus cyanogriseus IFM 11549 was investigated. Spectroscopic analysis coupled with photo- and O2-induced conversion revealed that BE-14106 and the heronamides had the same stereochemistry. BE-14106 showed potent growth inhibition against fission yeast cells with an MIC value of 0.50 μM (0.21 μg/mL), being 4 times less potent than heronamide C, which revealed the importance of the structure of the hydrocarbon tail for the activity.
3. Draft Genome Sequence of Streptomyces niveus NCIMB 11891, Producer of the Aminocoumarin Antibiotic Novobiocin
Katrin Flinspach, Christian Rückert, Jörn Kalinowski, Lutz Heide, Alexander Kristian Apel Genome Announc. 2014 Jan 9;2(1):e01146-13. doi: 10.1128/genomeA.01146-13.
Streptomyces niveus NCIMB 11891 is the producer of the gyrase inhibitor novobiocin, which belongs to the aminocoumarin class of antibiotics. The genome sequence of this strain was found to contain, besides the gene cluster for novobiocin, a putative gene cluster for the macrolactam antibiotic BE-14106 and further secondary metabolite gene clusters.

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